The Extortionist

Scott Boras, the Yankees’ bête noire, has changed baseball forever.

Boras and his client Alex Rodriguez, the Yankees’ third baseman, whom he has made the top-grossing athlete in team sports.Credit MARK ULRIKSEN

Scott Boras has season tickets to see the Dodgers, the Angels, the Padres, the Giants, and the A’s—a full California sweep. In Los Angeles and Anaheim, he also maintains luxury boxes, but, for the most part, wherever he goes he sits, or sometimes stands, in one of the first few rows directly in back of home plate, cell phone at his ear. Boras represents baseball players—among them the Yankees’ Alex Rodriguez (A-Rod), the top-grossing athlete in team sports, Barry Zito, the beneficiary of the largest pitching contract ever signed, and the Mets’ Carlos Beltran. Before a game, players will tend to approach the backstop and, in Boras’s telling, thank him for the work he does on their behalf. They needn’t even be his clients. (Ballplayers are firm believers in trickle-down economics.) Groundskeepers, umpires, and reporters, too, regularly drop by to pay their respects, trading anecdotes for scoops and the feeling of proximity to power. They shake his hand—fingers poking through the protective netting—without quite getting a firm grip.

To the extent that lay people still find it offensive when baseball players command salaries equivalent to those of movie stars and underperforming hedge-fund managers, Boras is a convenient bogeyman, and at every ballpark there are bound to be a few hecklers who let him know it. He was brought up Catholic, and, as he told a newspaper reporter earlier this year, “Being Catholic, who you are as a person, you don’t appreciate any association with Satan.” Still, there is a devilish turn to his smile—a glint of righteous defiance—and if there is a popular association that genuinely troubles him it is more likely that of Jerry Maguire, the smooth-talking Tom Cruise character, whom he does not at all resemble. Maguire is an agent. Boras is an attorney—a master of fine print, not histrionics. You won’t find him in a bar with his clients (he prefers the working breakfast), or pleading with them in the locker-room showers. He wears his thinning brown hair combed perfectly across his scalp, left to right, and his clothes are overdeliberate California casual: pressed jeans, polo shirt fully buttoned. Spontaneity has not recently occurred to him. Out of superstition, or some symbolic show of authenticity, he has carried the same beat-up leather satchel for years.

“People call me from the outside world all the time—they want me to negotiate everything,” Boras says, with a hint of irritation. “I’m not the person who will go out and negotiate anything, at any time, for anyone who happens to wear some sort of uniform.” He regards his nominal colleagues—the three hundred-odd agents who have been certified by the Major League Baseball Players Association, and many of whom represent athletes in several sports—as glorified valets. “You have to distinguish between someone who has a sales personality versus someone who is substantive, and has a form of legal practice representing individuals who just happen to play a singular sport, baseball,” he says. Like a celebrity criminal-defense attorney, Boras serves his rich and cosseted clientele with a high-minded sense of purpose, and he has little use for the notion that his tenacity as an advocate is a reflection of soulless greed. (An old baseball acquaintance of his, George Kissell, likes to joke that only eight people will attend Boras’s funeral—“and all eight will be pallbearers.”) In fact, Boras is a moralist—he sometimes calls himself the only Democrat in Orange County—and prone to lecture about capitalism and education and the larger meaning of it all. (“I see grand houses of symphonies and performing-arts centers and such, which is great for a community to have, but on the other hand I walk four blocks away and I see a run-down school and I’m wondering, Where are our priorities?”) When he talks about baseball, he likes to diagnose the state of the game. “We have no leadoff hitters anymore,” he once told me, laying part of the blame on veiled racial discrimination by the N.C.A.A. And, “The eradication of steroids is, frankly, not that noticeable.”

Last December, at Baseball America’s annual banquet, Boras was named the game’s most influential non-player in the twenty-five years since the magazine began publishing, beating out the current Major League Baseball commissioner, Bud Selig, who had recently declared the sport to be in its “golden age,” as well as Don Fehr, the longtime head of the Players Association. (The most influential player was Barry Bonds, who is a former Boras client, and similarly regarded.) “I could kind of feel in the room that it was, like, ‘What is this? Why is this guy up here? We’re baseball people,’ ” Boras recalls. The banquet is traditionally a feel-good event for management types, with a charitable focus and an emphasis on youth coaching and mentorship. Boras took the stage and delivered a sermon on economics. “What I told them all was: ‘You know what this business is about, guys? We’ve gone from, when I came into it, an industry that made, economically, about five hundred million dollars, and we went to a billion in 1990. We went to three billion in 2000. And now we’re near six billion in 2007. What it says for all of us in this room is this: We’re doing a good job with the game. We’re growing the game, as it should be grown. There’s a balance that’s needed in the growing of the game, and I provide the balance on one side, and you provide it on the other.’”

The applause was tepid. “You just wanted to crawl behind the curtain,” a Baseball America contributor told me. One National League manager considered walking out, in protest. And yet influence, however coolly embraced, can be infectious. Boras, who is fifty-four, seems to have become impatient with mere balance-provision. This spring, he mailed a letter to Commissioner Selig, in which he outlined a proposal to alter the format of the game’s most sacred ritual, the World Series. Why not make it nine games, instead of seven, he argued, and hold those extra two games—the first two games—at a neutral site? Cities all over the nation, or even the world, could compete for the honor of playing host, as with the Olympics. “It’s a fact that our game needs a forum that’s akin to the Super Bowl,” Boras explained to me not long after he’d sent the letter. “People don’t go to the Super Bowl for the game. Most Super Bowl games are not competitive, or good games. They go there for the event. They go there for the three-day weekend.” He described a vision of “corporate hospitality,” including a “gala, like the Oscars,” during which the M.V.P. and Cy Young awards, among others, would be announced, with all the finalists present and on view, and presumably walking the red carpet in sponsored menswear. Who could argue against such a change? It would mean more money for the owners, more “marketable content” for the media to broadcast, more attention for the stars—more everything.

“He takes himself very seriously,” Fay Vincent, the former commissioner, said recently of Boras. “I’m not surprised that he’s beginning to make grandiose suggestions.” Vincent added that he thought this particular World Series suggestion was “preposterous,” and, giving voice to a common complaint of fans and players alike, he said, “I mean, the season goes on endlessly as it is.”

Marvin Miller, the pioneering Players Association chief, was more acerbic. “That’s a typical example of an agent forgetting what his real role is,” Miller said. “He has no function whatsoever in suggesting a change in scheduling. He has absolutely nothing to say about it—not now or ever. But it’s quite typical. It’s a joke.”

These comments preceded by a few months the rumor that Boras was planning to arrange for an unprecedented deal, in which Alex Rodriguez would opt out of his contract with the Yankees, under whose terms he is already paid millions more than any other player, to become part owner of the Chicago Cubs. Rodriguez is thirty-two, and has never played in a World Series game—his gifts have thus far been suppressed in the post-season. Boras believes that he will play until he is forty-five, or long enough to eclipse the career records for hits, home runs, runs batted in, and runs scored, and that he deserves a new compensation package to match such legendary feats. Boras’s timing couldn’t be better: the Rodriguez standoff has coincided with the seeming implosion of the Yankees, beginning with the loss, last week, of their manager, Joe Torre.

Boras was a ballplayer himself until a series of knee operations ended his career, when he was twenty-six, and still in the minor leagues. Now, almost thirty years later, he has the thick torso and the stiff gait of a former jock, and, according to conventional dugout psychoanalysis, his resentment over not having made it to the Show is palpable—it’s what drives him to milk team owners, as stand-ins for the baseball gods, for all the money he can get. But the story of his life, as Boras views it, is a blessed one. Far from feeling betrayed by baseball and its old-boy network of colluding, miserly owners, he believes that he was treated consistently well at every stage of his career, and benefitted from the kind of mentoring that arises from generosity of spirit rather than from contractual obligation. Boras sees the fact that he ultimately failed as a player—that unlucky circumstances intervened to spoil his dream—as an instructive lesson about the harsh odds of the business, not as cause for any personal vendetta.

He grew up on an eight-hundred-acre farm near Elk Grove, California, about fifteen miles from Sacramento. His family raised dairy cattle and, later, cultivated alfalfa and oat hay. As a boy, driving a tractor, Scott listened to San Francisco Giants games called by Russ Hodges and Lon Simmons on KSFO, but he didn’t attend his first major-league game until 1968, when he was fifteen and, by then, a star high-school center fielder—a gap hitter with uncommon plate discipline.

Boras was a strong student—a scholar-athlete in the original, irony-free sense of the phrase—and he spurned inquiries from Ivy League schools, which he couldn’t afford, in favor of a scholarship to the University of the Pacific, in nearby Stockton, just outside San Francisco. He majored in chemistry, and the school arranged for him to take private labs after practice, from nine o’clock to midnight. “I was the first athlete to ever have, like, a pre-med-type situation,” he told me. After his sophomore year, he applied to a graduate program in industrial pharmacology and was accepted, and began working toward his doctorate concurrently with his B.A. “They told me I’d be the only athlete to be able to go to a professional school and play,” he said.

At Pacific, Boras thrived, eventually becoming team captain. He blames a collision with a fellow-outfielder near the end of his college career, which marked the beginning of his knee problems, for the fact that he was never drafted, but in 1974 he was signed as an amateur free agent by the St. Louis Cardinals organization, receiving an eight-thousand-dollar bonus, which he used to pay for his continuing education. Over the next three years, Boras would leave school four weeks early and return four weeks late in order to play professional baseball, taking his final exams during spring training under the supervision of a pair of leathery coaches, Ken Boyer and Jack Krol. “I’d buy ’em two six-packs of beer and they would proctor my exams,” he told me. “It was difficult, because you didn’t want to be held out to be a college boy—that was not a good thing then. And so when I studied on the bus I’d cover up my neuropharmacology book in a men’s magazine so that no one knew.”

The business of baseball was changing, and, with the elimination, in 1976, of the reserve clause, which enforced a kind of indentured servitude, it was soon transformed. The average major-league player at the time made forty-six thousand dollars a year, or sixty per cent as much as the average pro hockey player, and the richest baseball player, Dick Allen, earned two hundred and twenty-five thousand. (Today, the league minimum is three hundred and eighty thousand, and the average is close to three million.) Minor leaguers, meanwhile, began at four hundred and fifty dollars a month. Boras, as he started out, held no particular convictions about labor law or just compensation—“When I played baseball, I always felt it was such a privilege,” he says—but he seemed to have an innate sense of leverage. After he led the Class A St. Petersburg Cardinals in batting, he insisted that he be paid more than the next-highest hitter, on principle. And, once he finished his graduate studies, he renegotiated upward again. “I told them, ‘I’m going to have to consider leaving, because I can go out in the real world and make ten times what I can make playing baseball.’ ”

He’d had a revelation, one spring morning, as he watched forty-five players react to being cut, all at once. “I saw, in the parking lot, wives crying, even players crying,” he said. “I never expected that. I was blind to it when I came in. No one ever discloses to the players what’s going to happen to ninety-nine per cent of them, because less than one per cent of the players are going to have a six-year major-league career. And maybe as many as only three or four per cent are going to have a three-year career. And so the answer is that this is not a career—this is a trapdoor.”

The head of the Cardinals’ farm system, Bob Kennedy, was a “true gentleman,” Boras recalls, who seems to have recognized that Boras, even as his knees worsened, could prove valuable as a role model for less disciplined players. “Bob was one of the few guys in the baseball community who knew of my educational background,” Boras says. “He would ask me to talk to players all the time, and make sure that we set an example on the teams I played for.”

In 1977, Kennedy left to become the general manager of the Chicago Cubs, and shortly afterward he traded for Boras, who by that point was thinking of quitting. He told Kennedy that he was planning to go to law school, and Kennedy agreed to pay him for another year anyway. He was making about twelve hundred dollars a month. He didn’t play a single game in 1978, because of his knees, but he used his earnings, once again, to help pay for school.

He went to McGeorge, the law school at Pacific, where Supreme Court Justice Anthony Kennedy, then an appeals-court judge, taught constitutional law. (Boras, who says that he has never been able to write well, preferred remedies and tort reform.) While there, he sought out as an adviser a man by the name of Don Wollett, whose father had played minor-league baseball, and who specialized in labor law, serving as an arbitrator for the Teamsters in California. Wollett told Boras, “If you’re good at what you do in the practice of law, ninety per cent of what is said about you will be negative.”

Boras got his law degree in 1982, and took a job with the Chicago firm Rooks, Pitts & Poust, doing medical-malpractice work, in which he defended drug companies against class-action suits—arguably an even less popular job, in the public consciousness, than representing A-Rod. But baseball seemed to follow him even as he set about leaving it behind. During his job hunt, he had interviewed with a dozen different firms around the country, and had had a recurring experience. “I sat down, they looked at my résumé—I have twelve years of schooling—and what do they want to talk about?” he said. “Baseball.” A few old teammates, meanwhile, had begun asking him for legal advice in their dealings with management.

In February of 1985, Boras helped the relief pitcher Bill Caudill sign a five-year contract with the Toronto Blue Jays. The deal, which gave Caudill seven million dollars, making him the second-wealthiest reliever in baseball, was struck just eight minutes before a scheduled salary-arbitration hearing, and established Boras’s reputation for unflinching resolve. The next week, his picture appeared in Sports Illustrated. The partners of his firm called him in for a meeting: he’d have to choose between the drug companies and baseball. With the blessing of his wife, Jeanette (who, according to family lore, rebuffed his requests for a first date through six months of hard negotiating), he decided to hang out his own shingle. “I enjoyed working for people instead of big companies,” he says. “It’s like you’re working for David against Goliath.” The following year, Boras made Sports Illustrated again, this time for hiring an airplane pilot to fly over Toronto’s Exhibition Stadium while towing a message for the Blue Jays’ manager, Jimy Williams: “JIMY—GIVE CAUDILL THE BALL.”

Today, the Boras Corporation, which is based in Newport Beach, California, employs about seventy-five people, and includes several subsidiaries: Boras Sports Marketing, the Boras Sports Training Institute, and a personal-management and consulting firm. Scouts stationed in Venezuela, the Dominican Republic, Japan, and across the United States identify and recruit potential clients. (Bill Caudill is one of these, based in Seattle.) “His practice is a long, never-ending troop surge,” the veteran agent Tom Reich told me.

Boras represents sixty-five major-league players and about the same number of minor-league prospects, nearly all of whom he is apt to describe, at one time or another, as “special,” “unique,” “out of the box,” “once in a decade,” or, in the recent case of Alex Rodriguez, “IPN” (pronoun “eye-pin”), which is short for Iconic magnetism, historic Performance, and Network value. (Baseball insiders make sport of tracking Boras’s latest terms of art.) He takes a five-per-cent commission on the salaries of his major-league clients, which this year total two hundred and ninety-five million dollars, and on the signing bonuses of his prospects (but not on their paltry minor-league wages). Even the larger agencies, like C.A.A., Octagon, and the Beverly Hills Sports Council, do not at the moment have stables of baseball clients with guaranteed future contracts in excess of a billion dollars, as Boras does. He vows that he will never sell out to a “Hollywood agency,” despite having received offers that he says run to nine figures. “I’ve always wanted to be the best at something, and if you want to be the best at something I think you have to be very myopic at what you choose to pursue,” he told me. Being the best agent means that Boras’s current annual take-home, after expenses, is still far less than that of his veteran clients.

Boras is best known for his representation of Rodriguez—or, more specifically, for securing, in 2000, a ten-year, two-hundred-and-fifty-two-million-dollar deal for Rodriguez with the Texas Rangers, after which it emerged that the next-highest bidder had offered at least fifty million less. No baseball player, up to that point, had ever earned an annual salary of twenty million dollars, let alone twenty-five, and the sum of the contract was greater than what the Rangers’ owner, Tom Hicks, had spent in buying the entire franchise from a group of investors led by George W. Bush in 1998. After just three years, Hicks and his advisers decided that he could no longer afford Rodriguez—so much so that they were willing to pay almost ten million dollars a year to the Yankees for the privilege of not having to pay the other fifteen million. The Texas signing became a case study at Harvard Business School. (Under the heading “Rodriguez and Revenue”: “They believed that even after Rodriguez retired, his value and presence would still stay with the team.”)

Boras told me that, in the fall of 2000, as he was preparing for Rodriguez’s free agency, a producer from ESPN approached him about filming the negotiation process. “I looked at the producer and I go, ‘Who in their right mind would ever do such a thing, to disclose the intimate negotiations between you, the people you deal with every day, the teams, and everything?’ And he called me a day later and said, ‘Oh, yeah, Jeff Moorad’s going to do that.’ I’m going, like, ‘You found a pigeon that quickly?’ I was taken aback that anyone, particularly a lawyer, would ever do that.” Moorad, who is now the C.E.O. of the Arizona Diamondbacks, was then Boras’s biggest rival in the representation business, and, according to Jerry Crasnick, in “License to Deal,” a book about a year in the life of a self-loathing agent named Matt Sosnick, their competitiveness spilled over into the Newport Beach Little League. When Boras donated money to the program, and one of the local fields was renamed in his honor, Moorad bought the biggest outfield sign as an advertisement for his own firm. Moorad was also famous for throwing lavish All-Star Game parties, which Boras found distasteful and demeaning to the profession—just like the ESPN video segment, which showed Moorad fielding competing offers for the slugger Manny Ramirez and, eventually, settling on an eight-year, hundred-and-sixty-million-dollar deal, or the second-biggest contract in baseball history, after A-Rod’s. “That is the most staged, nonsensical thing,” Boras now says of the video. “Basically, the deal was done before the thing even started, so it was a hoax.” (Moorad disputes this characterization: “Watch it yourself.”)

Agents benefit from what business-school types refer to as “information asymmetry,” because they are in touch with multiple teams, who are, in turn, forbidden to communicate with one another. Controlling the flow of that information—between the teams, the media, and the players—is an essential component of the Boras methodology. “In terms of negotiation, this guy is an absolute special-forces guy,” a competitor said of Boras. “The prison interrogations—he’s one of those.” Boras is a skilled manipulator of the media, and shows the kind of patience, as deadlines approach, that derives from great self-confidence. (This spring, he cut his negotiations with the Arizona Diamondbacks over the pitcher Max Scherzer so close to the wire that the A.P. reported, at 4:42 A.M., “Diamondbacks fail to sign No. 1 pick Scherzer,” only to reverse course at 5:32 A.M., with a description of a four-year deal.) Boras is not, according to people familiar with his bargaining style, a yeller but, rather, a calm and even cartoonish condescender; in conversation, he comes across as someone who has never doubted his own dinner selection—although he would be happy to inform you of all the ways that you should doubt yours. Many of the veteran and more stubborn team executives are by now able to laugh him off (“Can you believe this arrogant prick?”), but it is not unheard of for younger officials to call around the league in need of being “talked down off the ledge,” as one recipient of such a call told me. A club official once resorted to removing his shoe and banging it on the table (“like Nikita Khrushchev,” Boras says), but no one has put a fist or a chair through a wall since the late nineties.

A cynic might suggest that Boras’s refusal to discuss, let alone display, his negotiating tactics may be more than principled discretion. For one thing, it could be a cover for his reputed “phantom offers,” such as the supposed six-year deal for Johnny Damon with which he reportedly tried to bait the Red Sox, in 2005. (When the Sox didn’t bite, Damon signed with the Yankees, for only four years.) A bluffer stands to gain nothing by showing his cards. But Boras, who says, “I don’t play cards,” is generally dismissive of all so-called insider accounts of baseball business dealings, and he slammed Michael Lewis’s best-selling “Moneyball,” about Billy Beane, the general manager of the Oakland A’s, for being “not quite as factual as we would like it to be.” He also told me that he would like to write a book of his own—about the art of self-negotiation, as he calls it, or reorganizing one’s priorities in order to reduce stress: “It just occurred to me that so much in America is focussed on time use of money, or money’s growth over time, but the reality of it is—what no one’s ever talked about—well, what if you lived twenty years longer?” He is looking for a ghostwriter with a background in geriatrics.

What Boras shows off, in lieu of poker skills, is his corporate headquarters—a sleek two-story building just off the Pacific Coast Highway, in the shadow of John Wayne Airport. The agency moved in a year ago, after investing fifteen million dollars in renovations and remodelling. Boras boasts that one of his clients told him the place feels like a locker room, but it resembles no locker room I have ever been in. Think of it as a spaceship that doubles as a museum. The exterior is all steel and glass, and the entrance is a giant windowless slab that’s been dimpled with softball-size impressions. It has no knob or handle, and swings open slowly, as though you were about to enter a crypt. The first things you see after stepping inside are abstract-art installations: a swirl of mounted Louisville Sluggers hovering below the ceiling and, straight ahead, an enormous vertical grid of perhaps a thousand baseballs. The halls are lined with trophy cases and life-size action posters of Greg Maddux, Jason Varitek, and other clients. The internal rooms and offices have been outfitted with multi-panel television displays and baseball-diamond-themed keypads for changing the channels, which have been renamed in honor of the corporation: BCTV1, BCTV2, and so forth. Even the cubicles have plasma screens. (“I go to his new office—and they have all these TVs,” Johnny Damon says.) One employee told me that the plan is eventually to have video highlights screening on an endless digital loop through the translucent walls; an electronic news ticker on the first floor has been customized to provide real-time updates on all of Boras’s clients.

Instead of an ordinary conference room, Boras has a “war room,” befitting his adversarial reputation, where the tables have been arranged in the shape of a giant V, facing a whiteboard. A panel outside the door identifies it as the Wollett Arbitration Room (W.A.R.), after Boras’s mentor at McGeorge, who used to help with arbitration cases. Such cases were formerly a strong suit of the Boras Corporation and are now, increasingly, a weakness—a casualty, perhaps, of overreaching. Boras has lost twelve of his last fifteen cases, thanks in part to his aggressively high filings, and also to combative efforts on the part of Major League Baseball, which arms individual teams with neatly compiled records of all the arguments that Boras has used in the past, many of which are contradictory. (Another side effect of his aggressiveness is that teams often choose to settle rather than risk the high cost of such an arbitration defeat.)

A dozen or so researchers sit together on the second floor, at desks stocked with statistical volumes and books by the analyst Bill James. One of their main jobs is to underscore the uniqueness of Boras’s upcoming free agents by producing three-ring binders full of Xeroxed spreadsheets and testimonials that can be mailed to potential suitors and the media. Boras calls these “treatises.” When I mentioned the binders recently to a high-level baseball executive, he broke out laughing. “I think it’s more to please the client,” he said. “Like, ‘Here’s a copy for you and your family to put above the fireplace.’ ” The famous A-Rod binder of 2000, which was reportedly printed in an edition of a hundred, at a cost of thirty-five thousand dollars, featured quotes, in large type, comparing Rodriguez to Michelangelo and Leonardo da Vinci, and made reference to how “handsome” and “charming” he is. Johnny Damon, whose binder included ten chapters and predicted that he would end up playing more games than any center fielder in history, says, “He made me feel like Ty Cobb.”

The basement, which is sometimes called the foxhole or the dungeon, has showers and a laundry room, for those working late, plus an oxygen-sealed computer room that houses the firm’s proprietary database—once a major selling point and now more of a stage prop, given the free availability of historical data on the Internet. Caterers bring in breakfast, lunch, and, when work demands, dinner, while a woman named Lilian Flores occasionally bakes sugar cookies in the kitchen for an afternoon snack. Staffers snack at their own risk, however, because Steve Odgers, a onetime strength coach with the Chicago White Sox, has prescribed diet plans and fitness regimens. Odgers runs the Sports Training Institute, which is housed off-site, on the campus of Soka University of America, about twenty minutes away. “It’s part of our culture,” Boras says. “Everybody works out.” During arbitration hearings, which are usually held in Florida or Arizona, Boras and a handful of his top deputies have been known to assemble in the hotel gym wearing T-shirts that read “Team Boras.”

Boras’s own office is sparsely decorated. When we first spoke, his assistant brought him a mug of hot tea, and he took a seat at the end of a long table in the middle of the room, facing his desk, which was paperless. “We’re purists about the game,” Boras told me. “We’re about commitment. We’re about making you better.” He brought up, as an example, Barry Zito, the San Francisco Giants’ lefty who is known almost as much for his surfer persona as for his sweeping curveball. “What we did with Barry Zito a year and a half ago is one of my better pieces of work,” he said. “It was really about getting him to be him. I call him Zicasso. The thing is, he wants to pitch powerfully, and I’m saying, ‘No, you’re Zicasso! You got to be the artist-poet-intellectual. That’s what you’re out there to do.’ He feeds off it. ‘You’re Zicasso. You come out and you paint!’ ” He added a wavelike flourish with his arm to punctuate each new mention of Zicasso—whose performance in the past couple of years, incidentally, has not been discernibly better than it was before.

This theme echoed a commencement speech that Boras gave at McGeorge, in 2002, where he estimated that his job was thirty per cent negotiating and seventy per cent performance improvement—coaching and counselling, essentially. There he told a story about a client who walked into his office for the first time in 1999, seeking to negotiate what seemed likely to be the last contract of his career. “I pointed out to him that I thought he was someone who could actually do more than what he’d done in his great career,” Boras said. “I could see his first thought was, Where’s the door?” He went on, “In this particular case, my advice was that there was nothing more this player could do once the game began. But his psychological preparation prior to each game might warrant a new approach.”

Boras retains a couple of psychologists, whose services are available to players free of charge—a perk that comes in handy when, say, their picture lands on the cover of the New York Post alongside a stripper from Las Vegas, such as occurred with Alex Rodriguez this year. (The Post’s headline: “STRAY-ROD.”) “We can find someone for them to talk to,” Jeff Musselman, a former Boras client who is now a Boras Corporation vice-president, explained the week after. “I’ve known Alex since he was in high school. These are things we talked about when he was young. If you’re going to be the best player in the league, these things are going to happen and you’ve got to know how to deal with them.”

In the commencement lecture, however, Boras was talking about Barry Bonds, who, as everyone in the audience knew, had just broken the single-season home-run record, with seventy-three. “We truly gave counsel that resulted in the betterment of the client—not only in a contract sense but in a performance sense, in a life sense,” he said. A year and a half later, the BALCO steroids scandal broke. Several months after that, Bonds switched agencies, and indicated in the San Francisco Chronicle that the split with Boras was not amicable. (Boras, in his office, said, “Philosophically, in areas that I can’t talk about, we were on different pages.”)

In “Game of Shadows,” the authors Mark Fainaru-Wada and Lance Williams describe a couple of instances in which Bonds’s strong will interfered with Boras’s legal work. Bonds wanted to sit in on contract talks, and once even called the San Francisco Giants’ owner, Peter Magowan, directly, for updates. At Boras’s urging, Bonds was at the time training and sharing his home with the slugger Gary Sheffield, another Boras client—and another BALCO witness. Sheffield, like Bonds, is known for his independence of mind, and he eventually ditched Boras in favor of representing himself. Sheffield and Boras are now entangled in a union grievance over the commission on a contract that Sheffield believes Boras had nothing to do with. Boras’s controlling style may be better suited for less self-assured stars, like A-Rod, or cheery, guileless players like Johnny Damon, who told me, of his relationship with Boras, “Scott for me was much like a psychologist this year. I was way into my head, and for the first time I had trouble with my legs. He makes you feel like you could play another ten years.”

At one point while I was in his office, Boras took a phone call, and explained afterward, “The draft is looming.” I asked if he planned to travel to Orlando, where the draft was being held. He smiled. “I think the draft is here,” he said. “It’s not in Orlando. We’re in the room”—he pointed up, toward the war room—“and we’re telling teams who they can draft, who they can’t. That’s basically how the thing goes.”

Until this year, baseball’s draft was merely a very long conference call, by the end of which more than one in every hundred eligible amateur players in the country had been selected—deceived into thinking that stardom was soon to follow. (The draft lasts fifty rounds, compared with seven in the N.F.L. and two in the N.B.A.) It was instituted in 1965, and remained largely unaffected by the steady advances of the Players Association over the next two decades. (Union membership is restricted to major-league players, who have consistently made concessions on the amateur end in exchange for increased freedom for veterans.) Boras first got involved in 1983, while still moonlighting as a baseball counsellor in the employ of Rooks, Pitts & Poust. That summer, he approached a tall pitcher named Tim Belcher, who had just finished his junior year at Mount Vernon Nazarene College, in Ohio, and had been selected No. 1 over all by the Minnesota Twins. College juniors were seen as highly exploitable, because of the quirks of N.C.A.A. eligibility rules. They had no bargaining leverage. The Twins initially offered Belcher eighty thousand dollars to sign, which was twenty thousand dollars less than Rick Monday had received in 1965, as the first pick in the first draft.

Boras noticed that Mount Vernon Nazarene was not in fact a member of the N.C.A.A., and belonged instead to a much smaller organization, the National Association of Intercollegiate Athletics, whose rules on eligibility were slightly different. He advised Belcher to plan to return to Ohio.

“The scouting director for the Twins was a very abrupt man,” Boras recalled in his office, referring to George Brophy, who died a few years ago. “He went public, saying, ‘It’s disgusting that these kids are being represented. They’re draft picks.’ All these antiquated thought processes. I kept on saying, ‘He’s a young man in a negotiation against a system, which requires him to sign a professional sports contract, which is governed by a collective-bargaining agreement. Why wouldn’t he need a lawyer?’ I said, ‘Why do your teams have lawyers who draft all these things up? You’ve unilaterally imposed all these rules.’ He sat there, looked at me, and goes, ‘I’m not a lawyer. I’m just talking to you about baseball. That’s not how we do things.’ I said, ‘Well, we’re changing. We’re changing for the betterment of the game. The great athletes aren’t going to come to baseball if you keep the bonuses at this level, because some owner will pay for that talent. It just happens to be in a different sport. Baseball players play football and basketball, too.’ ”

Boras contends that higher signing bonuses in those sports, where the college game is itself nearly professional, and where there is no illusion that prospective draftees are anything other than commodities, are partly to blame for the decline in African-American baseball players. (Blacks now account for only eight per cent of major leaguers, down from more than twenty-five per cent when Boras was still playing.) Belcher, however, was strictly a baseball player, and white. Brophy initially alleged that he had sacrificed his amateur status by hiring an agent; Boras countered that he was merely a legal adviser, and had signed no formal agreement. Belcher held out, returned to school, and reëntered the supplemental draft the next January, where he was taken by the Yankees. They paid him a hundred and twenty thousand dollars.

Repeat performances such as this in the intervening years have earned Boras the nickname Lord of the Loophole, and a number of teams, as a means of fighting back, have taken to automatically bypassing players affiliated with Boras. The league introduced “slot recommendations,” a form of price-fixing in which signing bonuses are preset, according to draft position, by the commissioner’s office, and owners wishing to pay out of lockstep must now justify their profligate intentions in writing. Fledgling agents, meanwhile, capitalize by using Boras’s reputation as a recruiting tool—“Sign with me, and the teams won’t punish you to get back at Scott.”

As Boras was recounting this history for me in his characteristically didactic fashion, a man dressed in jeans and an untucked striped shirt walked by his office window. “That’s Kurt Stillwell, by the way,” Boras said. Stillwell was the second over-all pick in that 1983 draft, after Belcher. He now works as a scout for Boras, based outside San Diego, and he had come to Newport to help man the phones for the 2007 draft, in which Boras was representing—or, rather, legally advising—seven of Baseball America’s twenty top-rated prospects. (“He’s like Wilt Chamberlain when he decided to pass more, and he led the league in assists,” a rival agent complained. “He decides to focus on the draft, and he gets fifteen of the thirty first-round picks.”) Later that afternoon, as I was heading to my car in the parking lot, I saw Stillwell and Boras and a couple of other retired major leaguers on the Boras Corporation masthead, Mike Fiore and Scott Chiamparino. They were all heading to Anaheim for the Angels-Twins game. Outside the office, among his fellow ex-ballplayers, Boras begins to shed his lawyerly guise and recover the jocular, teasing air of his playing days, and so there they were, Stilly and Scott and Champ and Fi, arguing over who was going to ride in whose Jeep or Range Rover. To some, this aspect of Boras’s personality is transparently vicarious. “He likes to use the fact that he played ball,” one rival says. “He played wiffle ball. I mean, he was in an organization, but he was no major-league player.”

The inaugural draft telecast, when it aired on ESPN2, a couple of days later, left no doubt about who is in control of the narrative. The word “signability”—code, basically, for the odds that a Boras client will return to school or take a sabbatical in an independent league—was repeated again and again by the hosts, who also interviewed the Hall of Famer Dave Winfield, a former three-sport athlete. Winfield said that if he were starting out today he might have to consider choosing another game. (Among other things, full college scholarships are relatively rare in baseball these days.) There was even a segment devoted to the “Boras Effect,” in which a couple of analysts explained his practice of simply stating a player’s worth in advance and warning teams not to draft him unless they planned to pay it. As a result, the Boras advisee Andrew Brackman, one of the top-rated pitchers, and a star basketball player as well (“two-sportability,” for those watching the telecast), fell to the deep-pocketed Yankees, with the thirtieth pick. They then gave him a signing bonus that was nearly a million dollars greater than the bonus given to the fourth over-all pick, the pitcher Daniel Moskos, by the resource-poor Pittsburgh Pirates. Kentrail Davis, an outfielder whom Boras had valued at “low-first-round money,” or about what the slot recommendation would have been for Brackman, was not chosen until the fourteenth round. Boras advised him to go to college instead.

One agent, who told me that he has instructed his staff to refer to Boras as “he who shall not be named,” then requested that his own name not be identified, for fear of recrimination from the union. “Gene Orza is a figurehead,” he said, referring to the chief operating officer of the Players Association. “Scott Boras is the union.”

Some of this paranoia is a function of the general ruthlessness and lawlessness of the industry, where the certification process is more or less perfunctory, and there is very little oversight. “As fiduciary systems go, it’s as bad as it gets,” an agent told me, and recommended that I look up the columns of the Daily News writer Bill Madden, who habitually refers to Boras as the “avenging agent.” The Madden fan added that Boras “stands for everything in the industry that’s gone to hell,” and, on being asked to elaborate, said, “It’s who he is, what he is, what his attitude is—it’s the kind of bastard he is.”

Matt Sosnick, in Jerry Crasnick’s book, accuses Boras of stealing a client of his, Jesse Foppert. When I asked Boras about the book, he said, “There’s this kid named Sosnick in it—some young kid who procures high-school players.” Sosnick is thirty-eight. “This book is written on the trials and tribulations of him saying, ‘I don’t know what I’m doing. I’m so proud of myself. I can get kids at eighteen to sign with me.’ And he’s still in business!”

Staying in business for too long can begin to wear on one’s conscience or nag at one’s pride—the indignity of being a valet. Boras’s earliest rival was an agent named Dennis (Go Go) Gilbert, another former minor leaguer, who got his start selling life insurance, door to door, in Hollywood. (Before he began representing ballplayers like George Brett and Jose Canseco, his clients included Michael Landon, Sally Field, and Rod Stewart.) He once drove a Rolls-Royce with “GOGO19” plates—a reference to his uniform number—but in 1999, after nearly twenty years as an agent, he quit the business, dedicated himself to the charity Reviving Baseball in Inner Cities (R.B.I.), and eventually resurfaced on the other side of the picket line, as a special assistant to Jerry Reinsdorf, the owner of the Chicago White Sox. “You have to understand, some people are in love with the game,” he told me, unapologetic about having switched allegiances. “You’re always going to find the White Sox have treated their players extremely well. We don’t overpay our players.” The White Sox have historically tended to avoid doing business with Scott Boras. Gilbert also pointed out that Joe Crede, a Boras client on Chicago’s roster, spent most of this season on the disabled list.

Gilbert’s management turn was followed, in 2004, by Jeff Moorad’s with the Arizona Diamondbacks, but both of them were really taking a worn trail of agent misgiving blazed by Jerry Kapstein, one of the pioneers of the trade, who in the early days of free agency represented stars like Carlton Fisk and Don Baylor and Fred Lynn, and was later decertified by the union after falling into bed with management: he married the daughter of Joan Kroc, the San Diego Padres’ owner. Kapstein then divorced, found God, began working with the homeless, and reëntered baseball as a senior adviser with the Red Sox. Today, he goes by Jeremy.

Boras’s yearnings do not extend in that direction (“I will never work for a team,” he says), though at times he seems to be trying to steer the ship from the shore, with ideas like the expanded World Series and, as he later explained to me, looking fifteen years down the line, a Pacific Rim Division, including teams in Seoul, Beijing, and Tokyo. “The footprint of baseball is already there,” he said. “I think the economics of the game will force us to strongly consider it.” A few months ago, he even called for the invention of a new statistic, the exceptional play, or E.P.—a way of rewarding “defensive acumen” that might also be useful in, say, bolstering the bargaining position of a free-agent star like Andruw Jones, who has suddenly lost his stroke at the plate.

Another, perhaps worthier plan of his, for which he hopes to enlist the support of Bill Gates, is to start a foundation—the paperwork has already been filed—dedicated to doubling the salaries of teachers, through a voucher-based system laden with incentives that would piggyback on existing contracts, like a public-private partnership. He says he doesn’t wish to supplant the teachers’ union; he’d merely bypass it, as he has done with the Players Association and the baseball draft. “I just think a lot of great minds that have gone into the teaching profession are leaving,” he says.

Boras says that his aim is to observe every team, including those on the East Coast, play at least nine games a year, which means that he must spend a great deal of time at the ballpark. He has a daughter, who is in college, and two high-school-age sons, both of whom play baseball. His house in Newport, which is set on a ridge overlooking the ocean, has a batting cage in the garage. “I don’t ever get bored with the game,” he told me. “I haven’t reached that point yet.” He then described his ideal day: lunch with a client, followed by watching his sons play baseball in the afternoon, and a trip to Angel or Dodger Stadium at night. (He and Jeanette share quality time at the gym each morning.) There are costs associated with such single-minded success. Boras says that he is an art and architecture lover, and he has paintings by Miró and Chagall to prove it, but he has never been to Europe. He referred to a recent four-day fishing trip with his family, during which he became violently seasick, as “a failed attempt at a vacation.”

The fishing trip came shortly before the All-Star break, which serves as a sort of annual convention for agents, with thirty teams’ worth of beat reporters swarming and all of the world’s best players—beware of client poachers—assembled in one place. This year’s game was held in San Francisco, and the city gave itself over to baseball, with free trolleys shuttling visitors between “FanFest” and the ballpark, and plenty of elaborate parties, including the union’s annual bash. The actor Robert Wuhl, who starred in “Arli$$,” the HBO show about a sports agent, showed up at the union event. (“That fucking Robert Wuhl,” Boras says. “I like him. But he had a show where he slept with his client’s wife. He’s asked me to go on that show. I said, ‘I will never go on that show.’ I said, ‘I hate that show.’ ”) Boras skipped all the parties, and in this respect, at least, he resembled Matt Sosnick, who told me, “I have enough trouble liking myself, let alone other agents.”

On the day of the game, I met Boras at A. T.& T. Park, around two o’clock, in his customary spot behind home plate, where he’d been holding court since 11 A.M. He was wearing jeans and a blazer, with a checked pink shirt, and shades. We retreated twenty or so rows, to a pair of seats shielded from the sun, where people no longer seemed to recognize that they were in the company of baseball’s preëminent power broker, who had recently begun floating a couple of related ideas: (1) that Alex Rodriguez, who was having a career year, might not wish to play out the remainder of his contract, which calls for three more years in New York; and (2) that the industry was ready to support thirty-million-dollar salaries.

Team Boras was well represented on the field, if not by its own high standards. “Last year, we had eight,” Boras said. “This year, I think we only have six.” (Those six included the batting leader and the home-run leader in each league.) He was still trying to sell his World Series idea, which the commissioner finally acknowledged during a town-hall chat with fans that afternoon. (“I know Scott Boras has made that suggestion,” Selig said. “I’m satisfied, quite frankly, that seven games—the system is working.”)

The previous day’s feature, the Home Run Derby, had been, to my mind, a tedious affair, so thoroughly dominated by commercial breaks and sideshows—Counting Crows performed in center field—that you could have confused its ostensible action for the batting practice we were now watching: sporadic bursts of long fly balls amid a scene of milling around. Boras saw the problem differently: the derby suffered from a lack of funding. “You know, the home-run-hitting contest shouldn’t be at the All-Star Game,” he said. “It should be at the end of the year. Players wouldn’t be worried about messing up their swings. A lot of them don’t care to participate, because there’s no incentive to do it, and in the middle of the season they care about their teams. But at the end they’re going to be fighting for something. And it’ll probably be corporately sponsored—there’ll be a check there for them, to really make this where players will be playing for something, like pro golf.” He added that he could envision a complementary exhibition, a skills competition for throwing and fielding, along the lines of basketball’s slam-dunk contest, but when, playing along, I suggested a base-stealing event, he balked. The players might hurt their legs.

Boras sounded hoarse, on account of a tour-de-force performance at “media day,” the previous morning, where he and a phalanx of five broad-shouldered associates held court for five hours in the lobby of the Westin St. Francis. Boras has said that he operates “in the arena of truth,” and, though he didn’t mean it as a form of self-criticism, the spacious confines of the metaphor seem apt. He has a way of bending and extending his facts into the outer reaches of plausibility. When I asked him how many staffers he’d brought with him to the All-Star Game, he said, “We have as many as ten people here.” Shortly thereafter, he said, “So we have about fifteen to twenty people here.” This followed a pattern he had established earlier, in Newport Beach, when enumerating the various departments and employees of the Boras Corporation, whose ranks swelled gradually from around seventy to more than a hundred. Critics of Boras call him a “compulsive liar,” or a “congenital liar,” while also granting that he, at least, seems to believe what he says. I prefer to think of it primarily as optimistic, adversarial embellishment, and, in the interest of illustrating that optimism, I will return to the subject of Barry Zito, whose début season with the Giants was not turning out to be worthy of the record-breaking money that enticed him to leave Oakland, and whose cerebral nature Boras was now attributing to his slow adjustment, implying that Zicasso would simply need more time.

Don Wollett, for whom the Boras war room was named, is now eighty-eight, and lives for much of the year on an island in Washington State, near the Canadian border, but last fall, before Zito’s move, he made it down to Oakland to watch a game with Boras and Zito’s father. “It was my only experience in a luxury box,” he told me recently. “I was very uncomfortable. I thought of my days in law school at the University of Chicago—the old Comiskey Park, in the bandbox bleachers. That felt more like real baseball.” Without criticizing Boras, he told me he was concerned about the game—about “the gross inequality in distribution of income” and “compensation unrelated to performance.”

Later, he sent me excerpts from a memoir he’d been working on. One passage read, “Baseball is a team game, not merely a collection of highly skilled personnel, some making a lot more money than others. And it is the performance of the team that governs success or failure. A sensible compensation system must reflect that fact. Paul Weiler, the Harvard labor-law professor, is correct when he argues that unrestrained free agency is not the best possible regime for professional baseball.” Another said, “I look at the Alex Rodriguez deal with the Texas Rangers and say to myself: ‘That’s great for you, Alex, Godspeed.’ But does this system make sense for our national pastime, in which, we like to think, performance is rewarded? It’s what you deserve, not what you can get, that counts.”

Ron Shapiro, a longtime baseball agent of a different stripe from Boras (he is the author of “The Power of Nice: How to Negotiate So Everyone Wins—Especially You!”), echoed Wollett’s sentiment this summer when he said that he believes his clients Cal Ripken, Jr., and Kirby Puckett benefitted, if not on the balance sheet, from forming lasting attachments with their respective teams and communities in Baltimore and Minnesota, where they played their entire careers. He brought up Alex Rodriguez by comparison. “I think that Alex still seems to be searching for something that lies beyond the pot of gold,” he said. “There’s something disquieting about his quest for acceptance.” This was before Cynthia Rodriguez, Alex’s wife, showed up at Yankee Stadium wearing a tight-fitting tank top with the words “Fuck You”—so much for lasting community attachments—printed on the back in gothic script. (The Post: “F-ROD.”) And then the Yankees, with their two-hundred-million-dollar payroll, flamed out in the first round of the playoffs for the third straight year, with Rodriguez doing nothing to shake his tabloid image as a world-beating choke artist.

The conventional wisdom in baseball circles, as the regular season neared its end, had been that Boras would dangle the threat of free agency to force the Yankees into a long-term contract extension for Rodriguez. Tom Hicks, the Texas owner, is still on the hook for about a quarter of the eighty-one million dollars the Yankees owe Rodriguez over the next three years, which means that he effectively costs them no more than Derek Jeter. (Few people recognize Boras’s responsibility, incidentally, for goading Rodriguez into making the taunting remarks in an old Esquire interview—“You don’t say, ‘Don’t let Derek beat you.’ He’s never your concern”—that set his Yankee tenure on an uneasy path from the start.) Brian Cashman, the Yankees’ general manger, said that he would not participate in an open bidding session should Rodriguez opt out, thereby annulling the Texas subsidy, and Boras is technically—“academically” and “theoretically” are the words he likes to use—forbidden to have discussions with other teams in the meantime, under the rules governing tampering.

But Boras is by nature a divorce lawyer, not a family mediator, which is why the Cubs rumor, as reported last month by New York, seemed so ingenious: Boras was supposedly in talks about a deal—a technically prohibited deal, as it turns out—that would have given Rodriguez a deferred ownership stake in the team, with civilians who also happened to be prospective owners of the Cubs, who are for sale. (“If it was true, that would be grounds to disqualify someone from becoming an owner before even filing the application,” the Yankees’ president, Randy Levine, protested.) “Great players with great demand create great rumors,” Boras said, in denying the account. But so do great agents, and Boras, using what the Atlanta Braves’ president, John Schuerholz, calls “voodoo economics,” has begun citing television ratings trends and revenue forecasts to suggest that Rodriguez is worth as much as eighty million dollars in annual cash flow, and therefore affordable to even the smallest of markets. (“When he presented us with that kind of offer with Andruw Jones, we found it so ridiculous and obnoxious we didn’t even respond,” Schuerholz said on ESPN Radio.) Boras compares Rodriguez to Wayne Gretzky (“Gretzky was an IPN player”), who, in 1988, halfway through a record-shattering hockey career, was sent from Edmonton to Los Angeles in an innovative deal that involved contributions from the concessionaires and the local cable network.

The deadline for declaring Rodriguez a free agent is ten days after the final game of the World Series. Last week, as the showdown began in earnest, Boras’s opt-out drama became caught up in a much grander, almost Shakespearean drama in Tampa, where the heirs of the doddering patriarch George Steinbrenner gathered, like Lear’s, to assert control of his kingdom. (The family’s first decision was to make Joe Torre an offer he could only refuse.)

Amid such distraction, Alex and Cynthia Rodriguez, after reportedly looking at a forty-million-dollar town house off Fifth Avenue (“STAY-ROD?”), were able to slip away for a family retreat of their own, under the protective custody of the Borases, in Newport Beach, while Boras’s research team put the finishing touches on a new, updated free-agent binder. The binder will include a section showing the poor post-season performances of such Hall of Famers as Willie Mays, Mickey Mantle, Joe DiMaggio, Yogi Berra, and Ted Williams. “Even Reggie Jackson, Mr. October, had four bad playoff series,” Boras told me.

“Academically, and theoretically, they could make an offer,” Boras said as the Steinbrenner claimants prepared to hash out the Yankees’ future. Then, speaking of Rodriguez, he switched to the past tense: “He enjoyed playing in New York.” ♦

Ben McGrath began working at The New Yorker in 1999, and has been a staff writer since 2003.